Ritz vs. Westin vs. something else

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I believe the Westin Casuarina has a dive shop on premise which is
I believe Red Sail ? I did not dive with them as I had a couple other
dive charters I wanted to try, so I cannot say one way or the other
on this particular charter. There is a small pool side restaurant
across the street called the sunshine grill, it is behind the sunshine suites hotel.
Very good burgers and tacos and a nice atmosphere ! Also as others have said,
stay within your training and comfort zone with your diving ! Tell any dive
charter what you're ok with and what you're not ok with and make sure they understand !
Be very careful when walking to different places it's very easy to
forget that they are driving on the opposite side of the street. It took me a day
or two to start looking in the right direction for traffic before crossing !
 
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I can't really help with the lodging as we stayed in condos but there are also some good shoredives that would be extremely interesting above 60'. Most have on-site dive operators so with a few e-mails/calls you could probably arrange for a DM at each.

Eden Rock comes to mind first - most of it is less than 40'. They have instructor/guides on staff just for the shore dives there.

Sunset House would be another option, the Amphitrite Mermaid statue is 51' at the base, a good photo-op, and there's a lot of shallow reef nearby. Really simple entry through their Saltwater pool out to the reef also. My Bar there for lunch is a diver's hangout.

North of 7MB is Turtle Reef. It's a short swim out from a protected cove - with a good ladder - to a shallow wall dive that doesn't exceed 50-60' in most places before it opens out into a sand flat. The wall is covered with stuff and there's usually Tarpon schooling in the shadows. Watch overhead, the channel is a shortcut to the North Wall so some big things often are seen - we saw a school of Eagle Rays fly by one dive. Sun Divers has the dive operation there.

The obvious, easy must-do is Stingray City. Most fun you'll have in 15' of water. Get up close and personal with a swarm of harmless Sting Rays. And there's usually a Moray Eel or two around. There's both a dive and a snorkel - do the dive.

For boat dives, Aquarium is a good choice, it's around 60' - drops deeper but where the mooring is is closer to 40' IIRC. And given the name, the fish life is profuse.

One other option is to go with one of the smaller charters and see if you're the majority on the boat. You might try Indigo Divers, they do 6pax maximum. Or Ambassador Divers, they'll go with as few as 2 from what I've read.

Just an observation, since you mentioned staying at the Ritz, you might look into a private charter also. They're really not that much more expensive and will do what you want. I think Indigo charters their smaller boat.

Other things for the boys to do: Boatswains Beach - Cayman's Adventure Theme Park. There's also the Butterfly Farm.

To add to what Idive2 just posted, if you rent a car watch out for the oblivious tourists, especially when the cruise ships dock downtown - we almost got two of them since they're focused on getting across the street to the shops and not looking the other way for approaching cars. My best suggestion is to stay out of downtown if you see a ship in the harbor. You'll have to go through town to get to Sunset House. Eden Rock is 100 yds. away from the cruise port so the best time to go there is mid-afternoon, still gives you time to dive but it won't be so crowded as no one wants to miss their sailing.
 
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